Cow–calf operations in grass-based agricultural systems in Marion County, Iowa, are multifunctional in their provision of agronomic, ecological, economic and social uses. Since 1992, however, pastureland and cow–calf operations have decreased because of urban encroachment, leading to a speculative loss of some beneficial functions. The goal of this interdisciplinary project, conducted from 2003 to 2005, was to employ a farming systems research and evaluation platform to investigate grassland multifunctionality at farm, field and community levels. A socio-cultural analysis was conducted with the objective of identifying motivations of cow–calf operators to remain on the land despite increasing urban pressure. Environmental, as well as socio-economic, parameters were evaluated in understanding grassland multifunctionality in semi-structured interviews and a focus group. Typology classes derived from the study placed the majority of participants as maintaining integrated cattle and grain operations as full-time income sources. At the farm and community levels, themes from participants’ responses suggested that the relevance of profit from a cow–calf operation is mediated by a wide range of livelihood and lifestyle choices, and that operators have diverse criteria regarding the suitability of land for pasture. Themes encompassing farm preservation and building intergenerational social capital were particularly evident among the full-time, integrated cattle/grain crop family farm members. At the community level, governmental policies rewarding practices that increase field and farm biodiversity, as demonstrated by a prairie pasture system implemented in a follow-up on-farm experiment, will facilitate greater support of grass-based systems from local institutions. In order to address the educational needs expressed by study participants, extension and federal environmental agencies are encouraged to provide relevant design and implementation recommendations in recognition of local knowledge related to farmland multifunctionality and sustainable land usage for integrated crop and livestock operations.